1. Field of the Invention
The present invention relates to a cyanurate compound containing three oxetane ring groups and an organic hardening composition containing the same. More particularly, the present invention relates to a photosetting or thermosetting cyanurate compound containing three oxetane ring groups, and an organic hardening composition containing the same.
The compounds having oxetane ring groups are photosetting or thermosetting monomers. The resins derived from the oxetane ring group-containing compounds generally exhibit excellent heat resistance, mechanical properties and adhesiveness. Thus, the oxetane ring group-containing compounds are useful as materials for shaped articles such as, for example, parts of electric devices, heat-resistant resists, coating materials and adhesives and as cross-linking agents and modifying agents for powder coating materials.
2. Description of the Related Art
Compounds containing oxetane ring groups (which will be referred to as oxetane compounds hereinafter) currently draw attention as cationically polymerizable monomers. Thus, various types of mono-functional or poly-functional oxetane compounds, for example, shown below have been reported.
(a) Pure Appl. Chem., A30 (2 &3), pp.189-206 (1993) discloses methods of synthesizing various oxetane compounds.
(b) DE Patent No. 1,021,858 discloses an oxetane compound represented by the formula (a): ##STR2##
wherein R.sup.2 represents an alkyl, aryl, aralkyl, cycloalkyl or di- or valent aromatic group; Et represents an ethyl group; and k represents an integer of 1 or 2.
(c) Japanese Unexamined Patent Publication No. 6-1.6804 discloses an oxetane compound of the formula (b): ##STR3##
wherein R.sup.3 represents a hydrogen or fluorine atom, or an alkyl group with 1 to 6 carbon atoms, a fluoroalkyl group with 1 to 6 carbon atoms, an alkyl group, an aryl group, or a thienyl group; R.sup.4 represents a multi-valent organic group selected from straight or branched chain poly (alkyleneoxy) groups, xylylene group, siloxane bond groups and ester bond groups; Z represents a oxygen or sulfur atom; and m represents an integer of 2 to 4.
(d) Japanese Unexamined Patent Publication No. 8-245,783 discloses a plurality of oxetane compounds, for example, di-functional oxetane compounds having a 2,2'-bitolylenediyl skeleton.
(e) Japanese Unexamined Patent Publication No. 9-309,950 and No. 10-212,343 disclose oxetane compounds of the formula (c): ##STR4##
wherein p represents an integer of 1 to 4;
R.sup.5 represents a hydrogen or fluorine atom or an alkyl group with 1 to 6 carbon atoms, an alkyl group, an aralkyl group, an aryl group, a furyl group or a thienyl group; R.sup.6 represents a hydrogen-atom when p is 1, or an organic group having a valence corresponding to the integer represented by p when p is 1 to 6; Z represents an oxygen or sulfur atom.
When the oxetane compounds are utilized as components of thermosetting resin compositions, the resultant thermoset resins are unsatisfactory in the heat resistance thereof. Particularly, in the field of the electronic materials, for example, resists, there is a strong demand for new type of oxetane compounds capable of forming thermosetting resin materials having excellent heat resistance.
In the prior art, no cyanuric acid derivatives having the oxetane ring groups and no synthetic methods for preparing the compounds were known.
Also, no organic hardening composition containing, as a hardening component, a cyanurate compound having the oxetane ring group was known before the present invention.